EP3428149A2 - Composé cyclique condensé et dispositif électroluminescent organique le comprenant - Google Patents

Composé cyclique condensé et dispositif électroluminescent organique le comprenant Download PDF

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EP3428149A2
EP3428149A2 EP18178737.5A EP18178737A EP3428149A2 EP 3428149 A2 EP3428149 A2 EP 3428149A2 EP 18178737 A EP18178737 A EP 18178737A EP 3428149 A2 EP3428149 A2 EP 3428149A2
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group
substituted
unsubstituted
aromatic
formula
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EP3428149B1 (fr
EP3428149A3 (fr
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Mieun Jun
Jongwoo Kim
Youngkook Kim
Seokhwan Hwang
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Samsung Display Co Ltd
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Samsung Display Co Ltd
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Definitions

  • the present invention relates to a condensed cyclic compound and an organic light-emitting device comprising the same.
  • Organic light-emitting devices are self-emission devices that have wide viewing angles, high contrast ratios, high brightness, low driving voltages, short response times, and many other excellent characteristics in terms of brightness, driving voltage, and response speed, compared to other display devices in the art.
  • An example of the organic light-emitting devices may comprise a first electrode disposed on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode, which are sequentially disposed on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, electrons provided from the second electrode may move toward the emission layer through the electron transport region, and when holes and electrons meet in the emission layer, they may recombine to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.
  • the present invention provides a condensed cyclic compound represented by Formula 1 below:
  • X 1 is selected from O, S, Se, C(R 4 )(R 5 ), Si(R 4 )(R 5 ), and B(R 4 ), rings A 1 , A 2 , and A 3 are each independently a C 5 -C 60 carbocyclic group or a C 2 -C 30 heterocyclic group, L 1 to L 9 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent
  • the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode, in which the organic layer comprises an emission layer and at least one condensed cyclic compound represented by Formula 1 described above.
  • the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; an emission layer disposed between the first electrode; a hole transport region disposed between the first electrode and the emission layer; and an electron transport region disposed between the emission layer and the second electrode, in which at least one of the hole transport region and the emission layer may comprise a condensed cyclic compound.
  • the condensed cyclic compound of this aspect comprises a tetracyclic structure comprising a 7-membered center ring and three fused side rings.
  • the 7-membered center ring comprises seven carbon atoms, or 6 carbon atoms and one of O, S, Se, Si and B atoms as ring members.
  • Each of the three fused side rings shares a two carbon border with the 7-membered center ring.
  • the three fused side rings do not share a border with each other.
  • the three fused side rings are each independently a C 5 -C 60 carbocyclic group or a C 2 -C 30 heterocyclic group, and one of the three fused side rings is linked to a tertiary amino group.
  • FIGS. 1-4 are intended for illustrative purposes, the elements in the drawings are not necessarily drawn to scale. For example, some of the elements may be enlarged or exaggerated for clarity purpose.
  • a condensed cyclic compound according to the present invention is represented by Formula 1 below:
  • X 1 in Formula 1 is selected from O, S, Se, C(R 4 )(R 5 ), Si(R 4 )(R 5 ), and B(R 4 ).
  • R 4 and R 5 are the same as described below.
  • X 1 in Formula 1 may be selected from O, C(R 4 )(R 5 ), Si(R 4 )(R 5 ), and B(R 4 ), but the present disclosure is not limited thereto.
  • Rings A 1 , A 2 , and A 3 in Formula 1 are each fused with a neighboring 7-membered ring, while sharing a two-carbon border therewith. Rings A 1 , A 2 , and A 3 in Formula 1 are each independently a C 5 -C 60 carbocyclic group or a C 2 -C 30 heterocyclic group.
  • rings A 1 , A 2 , and A 3 in Formula 1 may each independently be selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a pyrene group, a chrysene group, a triphenylene group, an indene group, a fluorene group, a benzofluorene group, a spiro-bifluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a pyrrole group, an imidazole group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a triazine group, an indenopyrazine group
  • rings A 1 , A 2 , and A 3 in Formula 1 may each independently be selected from a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a quinoline group, an isoquinoline group, a quinoxaline group, and a quinazoline group.
  • rings A 1 , A 2 , and A 3 in Formula 1 may each independently be a benzene group or a naphthalene group, but the present disclosure is not limited thereto.
  • L 1 to L 9 in Formula 1 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic C8 to C60 condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic 8- to 60-membered condensed heteropolycyclic group.
  • L 1 to L 9 in Formula 1 may each independently be selected from:
  • L 1 to L 9 in Formula 1 may each independently be selected from groups represented by Formulae 3-1 to 3-59 and 3-61 to 3-102:
  • d2 to d8 indicate the number of sites are substituted.
  • any d2 to d8 in any of Formulae 3-1 to 3-102 is two or more for any of the corresponding Z 1 and Z 2
  • two or more of the corresponding Z 1 (s) and Z 2 (s) may be identical to or different from each other.
  • the d4 for Z 1 in (Z 1 ) d4 may be 3, then 2 or 3 of these 3 Z 1 (s) may be identical, or all 3 are different from each other.
  • L 1 to L 9 in Formula 1 may each independently be selected from groups represented by Formulae 3-1 to 3-24, and
  • Z 1 to Z 7 in Formulae 3-1 to 3-24 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a dibenzofuranyl group, and
  • L 1 to L 9 in Formula 1 may each independently be selected from groups represented by Formulae 4-1 to 4-57:
  • Ph indicates a phenyl group
  • * and *' each indicates a binding site to a neighboring atom.
  • L 1 to L 9 in Formula 1 may each independently be selected from groups represented by Formulae 4-1 to 4-35, but the present disclosure is not limited thereto.
  • a1 to a9 are each independently an integer from 0 to 5.
  • a1 indicates the number of L 1 (s) in Formula 1, in which, when a1 is 0, *-(L 1 ) a1 -*' may be a single bond, and when a1 is two or more, two or more L 1 (s) may be identical to or different from each other.
  • a2 to a9 may be understood by referring to the description presented in connection with a1 above and the structure of Formula 1.
  • a1 to a9 in Formula 1 may each independently be 0, 1, or 2. In an exemplary embodiment of the present disclosure, a1 to a9 in Formula 1 may each independently be 0 or 1.
  • Ar 1 to Ar 6 in Formula 1 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic C8 to C60 condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic 8- to 60-membered condensed heteropolycyclic group.
  • Ar 1 to Ar 6 in Formula 1 may each independently be selected from:
  • Ar 1 to Ar 6 in Formula 1 may each independently be selected from groups represented by Formulae 5-1 to 5-50 and 6-1 to 6-124:
  • e2 to e7 anf e9 indicate the number of sites are substituted.
  • any e2 to e7 and e9 in any of Formulae 5-1 to 5-50 and 6-1 to 6-124 is two or more for any of the corresponding Z 31 to Z 34
  • two or more of the corresponding Z 31 (s) to Z 34 (s) maybe identical to or different from each other.
  • the e3 for Z 31 in (Z 31 ) e3 may be 3, then 2 or 3 of these 3 Z 31 (s) maybe identical, or all 3 are different from each other.
  • Ar 1 to Ar 6 in Formula 1 may each independently be selected from groups represented by Formulae 9-1 to 9-116 and 10-1 to 10-121:
  • Ph indicates a phenyl group
  • * indicates a binding site to a neighboring atom.
  • Ar 1 to Ar 6 in Formula 1 may each independently be selected from groups represented by Formulae 5-1 to 5-50 and 6-1 to 6-3 (for example, groups represented by Formulae 9-1 to 9-116 and 10-1 to 10-3).
  • b1 to b6 are each independently an integer from 1 to 5.
  • b1 indicates the number of Ari(s) in Formula 1, in which, when b1 is two or more, two or more Ari(s) may be identical to or different from each other.
  • b2 to b6 may be understood by referring to the description provided in connection with b1 above and the structure of Formula 1.
  • b1 to b6 in Formula 1 may each independently be 1 or 2. In an exemplary embodiment of the present disclosure, b1 to b6 in Formula 1 may each be 1.
  • R 1 to R 5 in Formula 1 are each independently selected from hydrogen, deuterium,-F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsub
  • R 1 to R 5 in Formula 1 may each independently be selected from:
  • R 1 to R 5 in Formula 1 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a mesityl group, and -Si(Q 1 )(Q 2 )(Q 3 ), in which Q 1 to Q 3 may each independently be selected from a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
  • R 1 to R 3 may each be hydrogen
  • R 4 and R 5 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a mesityl group.
  • c1 to c3 are each independently an integer from 0 to 5.
  • c1 indicates the number of R 1 (s) in Formula 1, in which, when c1 is two or more, two or more R 1 (s) maybe identical to or different from each other.
  • c2 and c3 may be understood by referring to the description provided in connection with c1 above and the structure of Formula 1.
  • c1 to c3 in Formula 1 may each independently be 0 or 1. In an exemplary embodiment of the present disclosure, c1 to c3 in Formula 1 may each be 0.
  • n1 to n3 are each independently 0 or 1, provided that the sum of n1, n2, and n3 is 1.
  • n1 indicates the number of groups represented by in Formula 1.
  • n1 and n2 may each be 0, n3 may be 1, n1 and n3 may each be 0, n2 may be 1, n1 maybe 1, and n2 and n3 may each be 0. That is, one amino group is comprised in the condensed cyclic compound. For example, one of rings A 1 , A 2 and A 3 is substituted with a tertiary amino group.
  • the condensed cyclic compound may comprise a tetracyclic structure which comprises a 7-membered center ring and three fused side rings.
  • the 7-membered center ring may comprise seven carbon atoms, or 6 carbon atoms and one of O, S, Se, Si and B atoms as ring members.
  • Each of the three fused side rings may share a two carbon border with the 7-membered center ring.
  • the three fused side rings may not share a border with each other.
  • the three fused side rings may each independently be a C 5 -C 60 carbocyclic group or a C 2 -C 30 heterocyclic group, and one of the three fused side rings may be linked to a tertiary amino group.
  • the condensed cyclic compound may be represented by one of Formulae 1A to 1C:
  • the condensed cyclic compound may be represented by one of Formulae 1-1 to 1-11:
  • X 1 may be O, S, C(R 4 )(R 5 ), Si(R 4 )(R 5 ), and B(R 4 ), L 1 to L 9 may each independently be selected from groups represented by Formulae 3-1 to 3-102 (for example, groups represented by Formulae 4-1 to 4-57), a1 to a9 may each independently be 0 or 1, Ar 1 to Ar 6 may each independently be selected from groups represented by Formulae 5-1 to 5-50 and 6-1 to 6-124 (for example, groups represented by Formulae 9-1 to 9-116 and 10-1 to 10-121), b1 to b6 may each be 1, R 1 to R 3 may each be hydrogen, and R 4 and R 5 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazon
  • the condensed cyclic compound may be represented by one of Formulae 1(1) to 1(18):
  • * in Formulae N-1 to N-41 indicates a binding site to a neighboring atom.
  • the condensed cyclic compound may be represented by one of Formulae 1(1) to 1(18), and R 4 , R 5 , and R m1 to R m13 in Formulae 1(1) to 1(18) may each independently be one of Compounds 1 to 3608 as shown in Table 1 below, but the present disclosure is not limited thereto:
  • H indicates hydrogen
  • Me indicates a methyl group
  • Ph indicates a phenyl group
  • Mes indicates a mesityl group.
  • the condensed cyclic compound represented by Formula 1 has a core A (see Formula 1' below).
  • the core A has a structure in which three ring groups are condensed with a 7-membered ring, and thus, structural stability may be enhanced. Also, hole transport and injection capability may be facilitated by changing the type of the ring group.
  • n1 to n3 are each independently 0 or 1, provided that the sum of n1, n2, and n3 is 1.
  • the condensed cyclic compound represented by Formula 1 may be a monoamine-based compound having one amino group. Accordingly, the condensed cyclic compound may have fast hole transport and injection capability. Therefore, an electronic device, for example, an organic light-emitting device, which comprises the condensed cyclic compound represented by Formula 1, may have a low driving voltage, high luminance, high efficiency, and a long lifespan.
  • At least one condensed cyclic compound represented by Formula 1 may be used between a pair of electrodes constituting an organic light-emitting device.
  • the condensed cyclic compound may be comprised in at least one layer selected from a hole transport region and an emission layer.
  • the condensed cyclic compound represented by Formula 1 may be used as a material for forming a capping layer positioned outside the pair of electrodes of the organic light-emitting device.
  • an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer comprising an emission layer, wherein the organic layer comprises at least one condensed cyclic compound represented by Formula 1.
  • (an organic layer) comprises at least one condensed cyclic compound represented by Formula 1" used herein may include a case in which "(an organic layer) comprises identical compounds represented by Formula 1", and a case in which "(an organic layer) comprises two or more different condensed cyclic compounds represented by Formula 1.”
  • the organic layer may comprise, as the condensed cyclic compound, only Compound 1.
  • Compound 1 may exist in an emission layer of the organic light-emitting device.
  • the organic layer may comprise, as the condensed cyclic compound, Compound 1 and Compound 2.
  • Compound 1 and Compound 2 may exist in an identical layer (for example, Compound 1 and Compound 2 may all exist in an emission layer), or in different layers (for example, Compound 1 may exist in an emission layer and Compound 2 may exist in a hole transport layer or a hole injection layer).
  • the first electrode of the organic light-emitting device maybe an anode
  • the second electrode of the organic light-emitting device may be a cathode
  • the organic layer of the organic light-emitting device may further comprise a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode.
  • the hole transport region may comprise a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof
  • the electron transport region may comprise a hole blocking layer, a buffer layer, an electron transport layer, an electron injection layer, or any combination thereof.
  • the hole transport region may comprise the condensed cyclic compound represented by Formula 1.
  • the hole transport region may comprise a hole transport layer, which comprises the condensed cyclic compound represented by Formula 1.
  • the hole transport region may comprise a hole injection layer, which comprises the condensed cyclic compound represented by Formula 1.
  • the present disclosure is not limited thereto.
  • the emission layer may comprise the condensed cyclic compound represented by Formula 1.
  • the emission layer may further comprise, in addition to the condensed cyclic compound represented by Formula 1, a host.
  • the emission layer of the organic light-emitting device may comprise a host and a dopant, wherein the host may comprise a fluorescent host and the dopant may comprise the condensed cyclic compound represented by Formula 1.
  • the present disclosure is not limited thereto.
  • the organic light-emitting device may further comprise at least one selected from a first capping layer disposed in a pathway along which light generated in an emission layer proceeds toward the outside through the first electrode and a second capping layer disposed in a pathway along which light generated in an emission layer proceeds toward the outside through the second electrode, and the at least one selected from the first capping layer and the second capping layer may comprise at least one of the condensed cyclic compounds represented by Formula 1.
  • the organic light-emitting device may have i) a stacked structure comprising a first electrode, an organic layer, a second electrode, and a second capping layer which are sequentially stacked in this stated order, ii) a stacked structure comprising a first capping layer, a first electrode, an organic layer, and a second electrode which are sequentially stacked in this stated order, or iii) a stacked structure comprising a first capping layer, a first electrode, an organic layer, a second electrode, and a second capping layer which are sequentially stacked in this stated order, and at least one selected from the first capping layer and the second capping layer may comprise the condensed cyclic compound represented by Formula 1.
  • organic layer refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of the organic light-emitting device.
  • a material comprised in the "organic layer” is not limited to an organic material.
  • FIG. 1 is a schematic view of an organic light-emitting device 10 according to an exemplary embodiment of the present disclosure.
  • the organic light-emitting device 10 comprises a first electrode 110, an organic layer 150, and a second electrode 190.
  • a substrate may be additionally disposed under the first electrode 110 or above the second electrode 190.
  • the substrate maybe a glass substrate or a plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
  • the first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on the substrate.
  • the material for the first electrode 110 may be selected from materials with high work function to facilitate hole injection.
  • the first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode.
  • a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and any combinations thereof, but the present disclosure is not limited thereto.
  • a material for forming the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combinations thereof, but the present disclosure is not limited thereto.
  • the first electrode 110 may have a single-layered structure, or a multi-layered structure comprising two or more layers.
  • the first electrode 110 may have a three-layered structure of ITO/ Ag/ITO, but the present disclosure is not limited thereto.
  • the organic layer 150 is disposed on the first electrode 110.
  • the organic layer 150 may comprise an emission layer.
  • the organic layer 150 may further comprise a hole transport region disposed between the first electrode 110 and the emission layer, and an electron transport region disposed between the emission layer and the second electrode 190.
  • the hole transport region may have i) a single-layered structure including a single layer which includes a single material, ii) a single-layered structure including a single layer which comprises a plurality of different materials, or iii) a multi-layered structure having a plurality of layers which comprise a plurality of different materials.
  • the hole transport region may comprise at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
  • the hole transport region may have a single-layered structure including a single layer which comprises a plurality of different materials, or a multi-layered structure having a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/ electron blocking layer structure, in which for each structure, constituting layers are sequentially stacked on and from the first electrode 110 in this stated order, but the present disclosure is not limited thereto.
  • the hole transport region may comprise the condensed cyclic compound represented by Formula 1.
  • the hole transport region may comprise a hole transport layer, which comprises the condensed cyclic compound represented by Formula 1.
  • the hole transport region may comprise at least one selected from 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris ⁇ N-(2-naphthyl)-N-phenylamino ⁇ -triphenylamine (2-TNATA), N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (NPB, NPD), ⁇ -NPB, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), Spiro-TPD, Spiro-NPB, methylated-NPB, 4,4'-cyclohexylidenebis[N,N-bis(m-MTDATA), 4,4',
  • R 201 and R 202 may optionally be linked via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group
  • R 203 and R 204 may optionally be linked via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.
  • L 201 to L 205 may each independently be selected from:
  • xa1 to xa4 may each independently be 0, 1, or 2.
  • xa5 may be 1, 2, 3, or 4.
  • R 201 to R 204 and Q 201 may each independently be selected from:
  • At least one of R 201 to R 203 in Formula 201 may each independently be selected from:
  • R 201 and R 202 may be linked via a single bond, and/or ii) R 203 and R 204 may be linked via a single bond.
  • At least one of R 201 to R 204 in Formula 202 maybe selected from:
  • the compound represented by Formula 201 may be represented by Formula 201A:
  • the compound represented by Formula 201 may be represented by Formula 201A(1) below, but the present disclosure is not limited thereto:
  • the compound represented by Formula 201 may be represented by Formula 201A-1 below, but the present disclosure is not limited thereto:
  • the compound represented by Formula 202 may be represented by Formula 202A:
  • the compound represented by Formula 202 may be represented by Formula 202A-1:
  • R 211 and R 212 are the same as described in connection with R 203
  • R 213 to R 217 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a
  • the hole transport region may comprise at least one compound selected from Compounds HT1 to HT39, but the present disclosure is not limited thereto:
  • a thickness of the hole transport region may be in a range of about 100 ⁇ to about 10,000 ⁇ , for example, about 100 ⁇ to about 1,000 ⁇ .
  • a thickness of the hole injection layer maybe in a range of about 100 ⁇ to about 9,000 ⁇ , for example, about 100 ⁇ to about 1,000 ⁇
  • a thickness of the hole transport layer may be in a range of about 50 ⁇ to about 2,000 ⁇ , for example about 100 ⁇ to about 1,500 ⁇ .
  • the emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer, and the electron blocking layer may block the flow of electrons from an electron transport region.
  • the emission auxiliary layer and the electron blocking layer may comprise the materials as described above.
  • the hole transport region may further comprise, in addition to these materials, a charge-generation material for the enhancement of conductive properties.
  • the charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
  • the charge-generation material may be, for example, a p-dopant.
  • the p-dopant may have a lowest unoccupied molecular orbital of about -3.5 eV or less.
  • the p-dopant may comprise at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but the present disclosure is not limited thereto.
  • the p-dopant may comprise at least one selected from:
  • R 221 to R 223 may each independently be selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic C8 to C60 condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic 8- to 60-membered condensed heteropolycyclic group, in which at least one selected from R 221 to R 223 may have at least one substituent selected from
  • the emission layer maybe patterned into a red emission layer, a green emission layer, or a blue emission layer, according to a sub-pixel.
  • the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other.
  • the emission layer may comprise two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.
  • the emission layer may comprise the condensed cyclic compound represented by Formula 1.
  • the emission layer may comprise a host and a dopant.
  • the dopant may comprise at least one selected from a phosphorescent dopant and a fluorescent dopant.
  • an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts based on 100 parts by weight of the host, but the present disclosure is not limited thereto.
  • a thickness of the emission layer may be in a range of about 100 ⁇ to about 1,000 ⁇ , for example, about 200 ⁇ to about 600 ⁇ . When the thickness of the emission layer is within this range, excellent light-emission characteristics maybe obtained without a substantial increase in driving voltage.
  • the host may comprise a compound represented by Formula 301 below: ⁇ Formula 301> [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
  • Ar 301 in Formula 301 may be selected from:
  • xb11 in Formula 301 is two or more, two or more Ar 301 (s) may be linked via a single bond.
  • the compound represented by Formula 301 may be represented by Formula 301-1 or 301-2:
  • L 301 to L 304 in Formulae 301, 301-1, and 301-2 may each independently be selected from:
  • R 301 to R 304 in Formulae 301, 301-1, and 301-2 may each independently be selected from:
  • the host may comprise an alkaline earth metal complex.
  • the host may be selected from a Be complex (for example, Compound H55 as shown below), a Mg complex, and a Zn complex.
  • the host may comprise at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds HI to H55, but the present disclosure is not limited thereto:
  • the phosphorescent dopant may comprise an organometallic complex represented by Formula 401 and a ligand represented by Formula 402 below: ⁇ Formula 401> M(L 401 ) xc1 (L 402 ) xc2
  • a 401 and A 402 in Formula 402 may each independently be selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an iso
  • X 401 may be nitrogen
  • X 402 may be carbon
  • both X 401 and X 402 may each be nitrogen at the same time.
  • R 401 and R 402 in Formula 402 may each independently be selected from:
  • two A 401 (s) in two or more L 401 (s) may optionally be linked via X 407 , which is a linking group, or two A 402 (s) may optionally be linked via X 408 , which is a linking group (see Compounds PD1 to PD4 and PD7 as shown below).
  • L 402 in Formula 401 maybe a monovalent, divalent, or trivalent organic ligand.
  • the phosphorescent dopant may be selected from, for example, Compounds PD1 to PD25, but the present disclosure is not limited thereto:
  • the fluorescent dopant may comprise the condensed cyclic compound represented by Formula 1.
  • the fluorescent dopant may comprise an arylamine compound or a styrylamine compound.
  • the fluorescent dopant may comprise a compound represented by Formula 501 below:
  • Ar 501 in Formula 501 may be selected from:
  • L 501 to L 503 in Formula 501 may each independently be selected from:
  • R 501 and R 502 in Formula 501 may each independently be selected from:
  • xd4 in Formula 501 may be 2, but the present disclosure is not limited thereto.
  • the fluorescent dopant may be selected from, for example, Compounds FD1 to FD22:
  • the fluorescent dopant may be selected from the following compounds, but the present disclosure is not limited thereto:
  • the electron transport region may have i) a single-layered structure including a single layer which includes a single material, ii) a single-layered structure including a single layer which comprises a plurality of different materials, or iii) a multi-layered structure having a plurality of layers which comprise a plurality of different materials.
  • the electron transport region may comprise at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but the present disclosure is not limited thereto.
  • the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, in which for each structure, constituting layers are sequentially stacked on and from an emission layer.
  • the present disclosure is not limited thereto.
  • the electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, and/or an electron transport layer in the electron transport region) may comprise a metal-free compound containing at least one ⁇ electron-depleted nitrogen-containing ring.
  • Examples of the ⁇ electron-depleted nitrogen-containing ring include an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an iso-benzothiazole group, a benzoxazole group, an isobenzoxazole group,
  • the electron transport region may comprise a compound represented by Formula 601: ⁇ Formula 601> [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
  • At least one selected from Ar 601 in the number of xe11 and R 601 in the number of xe21 may comprise the ⁇ electron-depleted nitrogen-containing ring.
  • ring Ar 601 may be selected from:
  • xe11 in Formula 601 is two or more, two or more Ar601(s) may be linked via a single bond.
  • Ar 601 in Formula 601 may be an anthracene group.
  • a compound represented by Formula 601 may be represented by Formula 601-1:
  • L 601 and L 611 to L 613 in Formulae 601 and 601-1 may each independently be selected from:
  • xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
  • R 601 and R 611 to R 613 may each independently be selected from:
  • the electron transport region may comprise at least one compound selected from, for example, Compounds ET1 to ET36, but the present disclosure is not limited thereto:
  • the electron transport region may comprise at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinolino)aluminum (Alq3), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum (BAlq), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ):
  • a thickness of the buffer layer, the hole blocking layer, or the electron control layer may be in a range of about 20 ⁇ to about 1,000 ⁇ , for example, about 30 ⁇ to about 300 ⁇ .
  • the electron blocking layer may have excellent electron blocking characteristics or electron control characteristics without a substantial increase in driving voltage.
  • a thickness of the electron transport layer may be in a range of about 100 ⁇ to about 1,000 ⁇ , for example, about 150 ⁇ to about 500 ⁇ . When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
  • the electron transport region (for example, the electron transport layer in the electron transport region) may further comprise, in addition to the materials described above, a metal-containing material.
  • the metal-containing material may comprise at least one selected from alkali metal complex and alkaline earth-metal complex.
  • the alkali metal complex may comprise a metal ion selected from a Li ion, a Na ion, a K ion, a Rb ion, and a Cs ion
  • the alkaline earth-metal complex may comprise a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Sr ion, and a Ba ion.
  • a ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be selected from a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but the present disclosure is not limited thereto.
  • the metal-containing material may comprise a Li complex.
  • the Li complex may comprise, for example, Compound ET-D1 (lithium quinolate, LiQ) or ET-D2:
  • the electron transport region may comprise an electron injection layer that facilitates injection of electrons from the second electrode 190.
  • the electron injection layer may directly contact the second electrode 190.
  • the electron injection layer may have i) a single-layered structure including a single layer which includes a single material, ii) a single-layered structure including a single layer which comprises a plurality of different materials, or iii) a multi-layered structure having a plurality of layers which comprise a plurality of different materials.
  • the electron injection layer may comprise an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof.
  • the alkali metal may be selected from, for example, Li, Na, K, Rb, and Cs.
  • the alkali metal may be Li, Na, or Cs.
  • the alkali metal may be Li or Cs, but the present disclosure is not limited thereto.
  • the alkaline earth metal maybe selected from, for example, Mg, Ca, Sr, and Ba.
  • the rare earth metal may be selected from, for example, Sc, Y, Ce, Tb, Yb, and Gd.
  • the alkali metal compound, the alkaline earth-metal compound, and the rare earth metal compound maybe selected from oxides and halides (for example, fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth-metal, and the rare earth metal.
  • oxides and halides for example, fluorides, chlorides, bromides, or iodides
  • the alkali metal compound may be selected from alkali metal oxides such as, for example, Li 2 O, Cs 2 O, and K 2 O, and alkali metal halides such as, for example, LiF, NaF, CsF, KF, LiI, NaI, CsI, and KI.
  • the alkali metal compound may be selected from, for example, LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but the present disclosure is not limited thereto.
  • the alkaline earth-metal compound may be selected from alkaline earth-metal oxides such as, for example, BaO, SrO, CaO, Ba x Sr 1-x O (0 ⁇ x ⁇ 1), and Ba x Ca 1-x O (0 ⁇ x ⁇ 1).
  • the alkaline earth-metal compound may be selected from, for example, BaO, SrO, and CaO, but the present disclosure is not limited thereto.
  • the rare earth metal compound may be selected from, for example, YbF 3 , ScF 3 , ScO 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 , and TbF 3 .
  • the rare earth metal compound may be selected from, for example, YbF 3 , ScF 3 , TbF 3 , YbI 3 , ScI 3 , and TbI 3 , but the present disclosure is not limited thereto.
  • the alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may comprise an ion of alkali metal, alkaline earth-metal, and rare earth metal as described above, and a ligand coordinated with a metal ion of the alkali metal complex, the alkaline earth-metal complex, or the rare earth metal complex may be selected from hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the present disclosure is not limited thereto.
  • the electron injection layer may comprise an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof, as described above.
  • the electron injection layer may further comprise an organic material.
  • an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof may be homogeneously or non-homogeneously dispersed in a matrix comprising the organic material.
  • a thickness of the electron injection layer may be in a range of about 1 ⁇ to about 100 ⁇ , for example, about 3 ⁇ to about 90 ⁇ . When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.
  • the second electrode 190 may be disposed on the organic layer 150 having above described structure.
  • the second electrode 190 maybe a cathode which is an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be selected from a metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function.
  • the second electrode 190 may comprise at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but the present disclosure is not limited thereto.
  • the second electrode 190 maybe a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
  • the second electrode 190 may have a single-layered structure, or a multi-layered structure comprising two or more layers.
  • FIGS. 2-4 each represents a schematic cross-sectional view of an organic light-emitting device, in which: an organic light-emitting device 20 of FIG. 2 comprises a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are sequentially stacked in this stated order; an organic light-emitting device 30 of FIG. 3 comprises a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are sequentially stacked in this stated order; and an organic light-emitting device 40 of FIG. 4 comprises a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are sequentially stacked in this stated order.
  • the first electrode 110, the organic layer 150, and the second electrode 190 may be understood by referring to the description presented in connection with FIG. 1 .
  • the organic layer 150 of each of the organic light-emitting devices 20 and 40 light generated in an emission layer may pass through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer 210 toward the outside, and in the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in an emission layer may pass through the second electrode 190, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer 220 toward the outside.
  • the first capping layer 210 and the second capping layer 220 may increase external luminescent efficiency according to the principle of constructive interference.
  • the first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer comprising an organic material, an inorganic capping layer comprising an inorganic material, or a composite capping layer comprising an organic material and an inorganic material.
  • the first capping layer 210 and the second capping layer 220 may each independently comprise at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrine derivatives, phthalocyanine derivatives, a naphthalocyanine derivatives, alkali metal complexes, and alkaline earth-based complexes.
  • the carbocyclic compound, the heterocyclic compound, and the amine-based compound may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I.
  • the first capping layer 210 and the second capping layer 220 may each independently comprise an amine-based compound.
  • At least one selected from the first capping layer 210 and the second capping layer 220 illustrated in FIG. 4 may comprise the condensed cyclic compound represented by Formula 1.
  • the first capping layer 210 and the second capping layer 220 may each independently comprise the compound represented by Formula 201 or the compound represented by Formula 202.
  • the first capping layer 210 and the second capping layer 220 may each independently comprise a compound selected from, for example, Compounds HT28 to HT33 and Compounds CP1 to CP5, but the present disclosure is not limited thereto:
  • the organic light-emitting device according to an exemplary embodiment of the present disclosure has been described in connection with FIGS. 1-4 .
  • the present disclosure is not limited thereto.
  • Layers constituting the hole transport region, an emission layer, and layers constituting the electron transport region may be formed in a certain region by using one or more suitable methods selected from, for example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.
  • suitable methods selected from, for example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.
  • the vacuum deposition maybe performed at a deposition temperature of about 100°C to about 500°C, at a vacuum degree of about 10 -8 torr to about 10 -3 torr, and at a deposition rate of about 0.01 ⁇ /sec to about 100 ⁇ /sec by taking into account the material to be comprised in a layer to be formed, and the structure of a layer to be formed.
  • the spin coating may be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80°C to about 200°C by taking into account the material to be comprised in a layer to be formed, and the structure of a layer to be formed.
  • C 1 -C 60 alkyl group refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms e.g. 1 to 30 carbon atoms, 1 to 20 carbon atoms, 1 to 10 carbon atoms, 1 to 6 carbon atoms or 1 to 4 carbon atoms. Examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.
  • C 1 -C 60 alkylene group refers to a divalent group having the same structure as the C 1 -C 60 alkyl group.
  • C 2 -C 60 alkenyl group refers to a hydrocarbon group having 2 to 60 carbon atoms, e.g. 2 to 30 carbon atoms, 2 to 20 carbon atoms, 2 to 10 carbon atoms, 2 to 6 carbon atoms or 2 to 4 carbon atoms, and at least one carbon-carbon double bond in the middle or at the terminus of the C 2 -C 60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group.
  • C 2 -C 60 alkenylene group refers to a divalent group having the same structure as the C 2 -C 60 alkenyl group.
  • C 2 -C 60 alkynyl group refers to a hydrocarbon group having 2 to 60 carbon atoms, e.g. 2 to 30 carbon atoms, 2 to 20 carbon atoms, 2 to 10 carbon atoms, 2 to 6 carbon atoms or 2 to 4 carbon atoms, and at least one carbon-carbon triple bond in the middle or at the terminus of the C 2 -C 60 alkyl group, and examples thereof include an ethynyl group, and a propynyl group.
  • C 2 -C 60 alkynylene group refers to a divalent group having the same structure as the C 2 -C 60 alkynyl group.
  • C 1 -C 60 alkoxy group refers to a monovalent group represented by -OA 101 (wherein A 101 is the C 1 -C 60 alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
  • C 3 -C 10 cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • C 3 -C 10 cycloalkylene group refers to a divalent group having the same structure as the C 3 -C 10 cycloalkyl group.
  • C 1 -C 10 heterocycloalkyl group refers to a monovalent monocyclic group having at least one heteroatom (e.g. 1, 2, 3, 4 or 5 hereoatoms) selected from N, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, e.g. 1, 2, 3, 4 or 5 ring carbon atoms. Examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group.
  • C 1 -C 10 heterocycloalkylene group refers to a divalent group having the same structure as the C 1 -C 10 heterocycloalkyl group.
  • C 3 -C 10 cycloalkenyl group refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.
  • C 3 -C 10 cycloalkenylene group refers to a divalent group having the same structure as the C 3 -C 10 cycloalkenyl group.
  • C 2 -C 10 heterocycloalkenyl group refers to a monovalent monocyclic group that has at least one heteroatom (e.g. 1, 2, 3, 4 or 5 hereoatoms) selected from N, O, Si, P, and S as a ring-forming atom, 2 to 10 carbon atoms, e.g. 2, 3, 4 or 5 ring carbon atoms, and at least one carbon-carbon double bond in its ring.
  • Non-limiting examples of the C 2 -C 10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group.
  • C 2 -C 10 heterocycloalkenylene group refers to a divalent group having the same structure as the C 2 -C 10 heterocycloalkenyl group.
  • C 6 -C 60 aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, e.g. 6 to 20 ring carbon atoms, 6 to 14 ring cabon atoms or 6 to 10 ring carbon atoms
  • a C 6 -C 60 arylene group used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms e.g. 6 to 20 ring carbon atoms, 6 to 14 ring cabon atoms or 6 to 10 ring carbon atoms.
  • Examples of the C 6 -C 60 aryl group are a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group.
  • the C 6 -C 60 aryl group and the C 6 -C 60 arylene group each comprise two or more rings, the rings maybe fused to each other.
  • C 1 -C 60 heteroaryl group refers to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom (e.g. 1, 2, 3, 4 or 5 hereoatoms) selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms, e.g. 1 to 19 ring carbon atoms, 1 to 13 ring cabon atoms or 1 to 9 ring carbon atoms.
  • C 1 -C 60 heteroarylene group refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom (e.g.
  • Examples of the C 1 -C 60 heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group.
  • the C 1 -C 60 heteroaryl group and the C 1 -C 60 heteroarylene group each comprises two or more rings, the rings may be fused to each other.
  • C 6 -C 60 aryloxy group indicates -OA 102 (wherein A 102 is the C 6 -C 60 aryl group), and a C 6 -C 60 arylthio group indicates -SA 103 (wherein A 103 is the C 6 -C 60 aryl group).
  • Detailed examples of the monovalent non-aromatic C8 to C60 condensed polycyclic group include a fluorenyl group and a spirobifluorenyl group.
  • divalent non-aromatic C8 to C60 condensed polycyclic group used herein, refers to a divalent group having the same structure as the monovalent non-aromatic C8 to C60 condensed polycyclic group.
  • the term "monovalent non-aromatic 8- to 60-membered condensed heteropolycyclic group" as used herein refers to a monovalent group having 8 to 60 ring-forming atoms (for example, 8 to 22, 8 to 18, 8 to 14 or 8 to 10 ring-forming atoms), having two or more rings condensed to each other, at least one heteroatom (e.g. 1, 2, 3, 4 or 5 hereoatoms) selected from N, O, Si, P, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure.
  • An example of the monovalent non-aromatic 8- to 60-membered condensed heteropolycyclic group is a carbazolyl group.
  • divalent non-aromatic 8- to 60-membered condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic 8- to 60-membered condensed heteropolycyclic group.
  • C 5 -C 60 carbocyclic group refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, e.g. 5 to 20 ring carbon atoms, 5 to 14 ring cabon atoms or 5 to 10 ring carbon atoms, in which all ring-forming atoms are carbon atoms.
  • the C 5 -C 60 carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group.
  • the C 5 -C 60 carbocyclic group may be a ring, such as benzene, a monovalent group, such as a phenyl group, or a divalent group, such as a phenylene group.
  • the C 5 -C 60 carbocyclic group maybe a trivalent group or a quadrivalent group.
  • C 1 -C 60 heterocyclic group refers to a group having the same structure as the C 5 -C 60 carbocyclic group, except that as a ring-forming atom, at least one heteroatom (e.g. 1, 2, 3, 4 or 5 hereoatoms) selected from N, O, Si, P, and S is used in addition to carbon (the number of carbon atoms is in a range of 1 to 60, e.g. 1 to 20 ring carbon atoms, 1 to 14 ring cabon atoms or 1 to 10 ring carbon atoms).
  • Heterocyclic group comprises one or more heterocyclic rings.
  • Ph represents a phenyl group
  • Me represents a methyl group
  • Et represents an ethyl group
  • ter-Bu represents an ethyl group
  • OMe represents a methoxy group
  • biphenyl group refers to a "phenyl group substituted with a phenyl group.
  • the "biphenyl group” is one of a “substituted phenyl group” having a "C 6 -C 60 aryl group” as a substituent.
  • terphenyl group refers to a "phenyl group substituted with a biphenyl group. That is, the "terphenyl group” is one of a “phenyl group” having, as a substituent, a "C 6 -C 6 aryl group substituted with a C 6 -C 6 aryl group.”
  • the condensed cyclic compound represented by Formula 1 may be synthesized by using a known organic synthesis method.
  • a synthesis method of the condensed cyclic compound may be recognizable by one of ordinary skill in the art in view of the following exemplary embodiments.
  • the reaction solution was cooled to room temperature, and an organic layer was extracted therefrom three times by using salt water, water, and diethylether.
  • the extracted organic layer was dried by using magnesium sulfate, and a solvent was evaporated therefrom.
  • the residue obtained therefrom was separated and purified by silica gel column chromatography to obtain 2.39 g (yield: 81%) of Compound 1363.
  • the obtained compound was identified by liquid chromatography/mass spectrometry (LC-MS) and 1 H nuclear magnetic resonance (NMR).
  • a Corning 15 ⁇ /cm 2 (1,200 ⁇ ) ITO glass substrate was cut to a size of 50 mm x 50 mm x 0.7 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the resultant ITO glass substrate was provided to a vacuum deposition apparatus.
  • 2-TNATA was vacuum-deposited on the ITO anode to form a hole injection layer having a thickness of 600 ⁇
  • Compound 126 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 ⁇ .
  • ADN 9,10-di-naphthalene-2-yl-anthracene
  • Compound FD1 dopant
  • Alq 3 was vacuum-deposited on the emission layer to form an electron transport layer having a thickness of 300 ⁇
  • LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 ⁇
  • Al was vacuum-deposited on the electron injection layer to form a second electrode (cathode) having a thickness of 3,000 ⁇ , thereby completing the manufacture of an organic light-emitting device.
  • Organic light-emitting devices of Examples 2 to 6 and Comparative Examples 1 to 3 were manufactured in the same manner as in Example 1, except that Compounds shown in Table 2 were each used as a material for forming a hole transport layer.
  • the driving voltage, current density, luminance, efficiency, and half lifespan of the organic light-emitting devices manufactured according to Examples 1 to 6 and Comparative Examples 1 to 3 were measured by using Keithley SMU 236 and a luminance meter PR650, and results thereof are shown in Table 2.
  • the half lifespan is an amount of time that had lapsed when luminance was 50% of initial luminance.
  • An organic light-emitting device comprising the condensed cyclic compound according to an exemplary embodiment of the present disclosure may have a low driving voltage, high efficiency, high luminance, and a long lifespan.

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